A boron-nitrogen-porphyrin compound and application thereof

Abstract

The present application provides a kind of boron-nitrogen-porphyrin compound and its application, the boron-nitrogen compound has the structure shown in formula I and formula II, the boron-nitrogen-porphyrin compound of the present application is based on the compound of boron-nitrogen and porphyrin construction.The boron-nitrogen-porphyrin compound of the present application has luminescent properties, as a luminescent material for preparing the light-emitting layer of organic electroluminescent device, the organic electroluminescent device prepared thereby realizes the emission of emission wavelength 600-800nm, and makes the highest external quantum efficiency of electroluminescence of device be as high as more than 10%.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology and relates to a boron nitrogen-porphyrin compound and its applications. Background Technology

[0002] Organic optoelectronic materials are a class of organic materials that possess properties such as the generation, conversion, and transmission of photons and electrons. Currently, the controllable optoelectronic properties of organic optoelectronic materials have been applied to organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), organic field-effect transistors (OFETs), and even organic lasers. In recent years, OLEDs have become a very popular new type of flat panel display product both domestically and internationally. OLED displays feature self-emissive characteristics, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panels, the ability to manufacture large-size flexible panels, and low cost, earning them the reputation as the star flat panel display product of the 21st century.

[0003] The history of organic electroluminescence can be traced back to the report by Bernanose et al. in 1953 (Holst GA, Kster T, Voges E, et al. FLOX—an oxygen-flux-measuring system using a phase-modulation method to evaluate the oxygen-dependent fluorescence lifetime, ScienceDirect. Sensors and Actuators B: Chemical, 1995, 29, 213.). About 10 years later, in 1963, Pope et al. of New York University observed the fluorescence emission of anthracene by applying a voltage to anthracene crystals (M. Pope, H. Kallmann and P. Magnante, Electroluminescence in Organic Crystals, J. Chem. Phys., 1963, 38, 2042). In 1987, CWTang et al. of Kodak Corporation in the United States used ultrathin film technology, employing aromatic amines with good hole transport performance as the hole transport layer, an aluminum complex of 8-hydroxyquinoline as the light-emitting layer, and indium tin oxide (ITO) thin film and a metal alloy as the anode and cathode, respectively, to fabricate a light-emitting device. This device achieved a brightness of 1000 cd / m² at a driving voltage of 10V.2 The green light emission of the device, with an efficiency of 1.5 lm / W (CWTang and S.A. Van Slyke, Organic electroluminescent diodes, Appl. Phys. Lett., 1987, 51, 913), was a breakthrough that led to the rapid and in-depth development of organic electroluminescence research worldwide. In 1990, Burroughes et al. of Cambridge University proposed the first light-emitting diode based on polymer (PPV). This showed that PPV, in monolayer devices, can serve as a highly fluorescent emitting material with high luminous efficiency (Burroughes J He et al., Light-emitting diodes based on conjugated polymers, Nature, 1990, 347, 539). In 1998, Baldo and Forrest et al. from Princeton University reported the first phosphorescent device based on electroluminescence, which in principle could have 100% internal quantum yield (MA Baldo, DFO' Brinetal., Highly efficient phosphorescent emission from organic electroluminescent devices, Nature, 1998, 395, 151). However, on the one hand, phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive. On the other hand, deep blue phosphorescent materials still have chemical instability and large efficiency roll-off problems at high current densities. Therefore, it is extremely important to develop an OLED device that can achieve high-efficiency light emission using inexpensive and stable small organic molecule materials.

[0004] In 2012, the Adachi research group at Kyushu University reported a highly efficient all-fluorescent OLED device based on the thermally activated delayed fluorescence (TADF) mechanism (Uoyama H, Goushi K, Shizu K, et al. Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, 2012, 492(7428):234-238.). When the energy difference between the S1 and T1 levels of a molecule is small enough, the triplet exciton can absorb thermal energy, return to the singlet state through the RISC process, and then emit fluorescence. Theoretically, the internal quantum efficiency (IQE) of the device can reach 100%, and the external quantum efficiency (EQE) can even reach 30%, comparable to the level of phosphorescent devices.

[0005] TADF molecules are mainly used as guest materials to dope in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (Q. Zhang, J. Li, K. Shizu, et al. Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes, J. Am. Chem. Soc. 2012, 134, 14706; H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Highly efficient organic light-emitting diodes from delayed fluorescence, Nature, 2012, 492, 234; T. Nishimoto, T. Yasuda, et al. A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluorescence OLEDs, Mater. Horiz. 2014, 1, 264). Carbazole-based boron nitrogen compounds are a class of TADF materials with narrow-spectrum luminescence properties, while porphyrin compounds are a class of classic luminescent materials containing metallic Pt. 2+ and Pd 2+ Porphyrin compounds exhibit phosphorescence emission properties. Summary of the Invention

[0006] The purpose of this invention is to combine carbazole-based boron nitrogen compounds with porphyrin compounds to provide a novel class of luminescent materials and their applications. The compounds provided by this invention aim to offer a novel luminescent material that can be used to prepare the light-emitting layer of organic electroluminescent devices, enabling these devices to exhibit excellent properties.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] On one hand, the present invention provides a boron-nitrogen-porphyrin compound having the structure shown in Formula I or Formula II:

[0009]

[0010] M represents Zn +2 Pt +2 Pd +2Ru +2 Os +2 Cu +2 Fe +2 C0 +2 [AlCl] +2 [GaCl] +2 [RuCl] +2 [OsCl] +2 [IrCl] +2 [FeCl] +2 [CoCl] +2 [LaCl] +2 [AlOH] +2 [GaOH] +2 [RuF] +2 [OsF] +2 [IrF] +2 [FeF] +2 [CoF] +2 Or [LaF] +2 ;

[0011] R 1 R 2 R 3 and R 4 Independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, and dominated by one or more R a Substituted C6-C18 aryl, 5- to 18-heteroaryl, and substituted with one or more R a Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R a Substituted diphenylamine group;

[0012] R a Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R b Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R b Substituted diphenylamine group;

[0013] R b Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R cSubstituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R c Substituted diphenylamine group;

[0014] R c Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R d Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R d Substituted diphenylamine group;

[0015] R d Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or is affected by one or more R groups. e Substituted C6-C14 aryl groups;

[0016] R e Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl;

[0017] R 1 R 2 R 3 and R 4 Independent existence or R 1 R 2 R 3 and R 4 At least one of them forms a ring with the connected aromatic ring;

[0018] R P1 R P2 R P3 R P4 R P5 R P6 and R P7 It is H, deuterium, F, C1-C18 alkyl, C6-C14 aryl, 5- to 24-membered heteroaryl or The asterisks represent bond sites;

[0019] R P1 R P2 R P3 R P4 R P5 R P6 and R P7 Independent existence or R P1 R P2 RP3 R P4 R P5 R P6 and R P7 At least one of them forms a ring with the connected aromatic ring;

[0020] The alkyl, alkoxy, cycloalkyl, aryl, or heteroaryl groups may be optionally substituted with one or at least two substituents selected from the following: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl.

[0021] Preferably, the R 1 R 2 R 3 and R 4 Independently H, deuterium, C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group;

[0022] Preferably, the R a Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group;

[0023] Preferably, the R b Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C12 Alkyl-substituted carbazole group;

[0024] Preferably, the R c Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group;

[0025] Preferably, the R d Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, carbazole, or alkyl-substituted phenyl groups with at least one C1-C bond 12 Alkyl-substituted carbazole group;

[0026] Preferably, the R 1 R 2 R 3 and R 4 Independently, it is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexoxy Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl

[0027]

[0028] The wavy lines represent the connection sites of the functional groups;

[0029] Preferably, the R 1 R 2 R 3 and R 4 Independently hydrogen, methyl, 2-methyl-phenyl, phenyl,

[0030] The wavy lines represent the connection sites of the functional groups.

[0031] More preferably, the R 1 R 2 R 3 and R 4 Independently for hydrogen, Preferably, R P1 R P2 R P3 R P4 R P5 R P6 and R P7 It is H, deuterium, methyl or tert-butyl.

[0032] In some embodiments of the present invention, the boron-nitrogen-porphyrin compound is any one of the following compounds:

[0033]

[0034]

[0035]

[0036]

[0037] On the other hand, the present invention provides an organic electroluminescent composition comprising a host material and a dopant material, wherein the dopant material comprises at least one of the boron nitride-porphyrin compounds as described above.

[0038] Preferably, the host material is a material having electron transport capability and / or hole transport capability and whose triplet excited state energy is equal to or higher than the triplet excited state energy of the doped material.

[0039] In one embodiment of the present invention, the doping material in the organic electroluminescent composition is any one of the boron nitrogen-porphyrin compounds of Formula I and Formula II; the host material is any one of the compounds shown in Formula Trz1-A, Trz2-A or Trz3-A;

[0040]

[0041] Z is either N or CH;

[0042] Where R z1 As for R z10 Independently hydrogen, deuterium, F, CN, C1-C8 alkyl, C1-C8 alkoxy, C6-C 30Aryl, R za Replacement C6-C 30 Aryl, C6-C30 heteroaryl or R za β-substituted C6-C 30 Mixed aromatics;

[0043] R za It is a C1-C8 alkyl, C1-C8 alkoxy, C6-C 24 Aryl or C6-C 24 Mixed aromatics;

[0044] R z9 Or R z10 Aromatic rings, either independently or connected to them, form a ring.

[0045] Preferably, the dopant content in the organic electroluminescent composition is 0.3wt%-15.0wt%, for example 0.3wt%, 0.5wt%, 1wt%, 2wt%, 3wt%, 5wt%, 8wt%, 10wt%, 13wt%, or 15wt%, and the content of the host material is 99.7wt%-85.0wt%, for example 99.7wt%, 95wt%, 93wt%, 90wt%, 88wt%, or 85wt%.

[0046] Preferably, the doping material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-48, and the host material is composed of any one of the compounds shown in formula Trz1-A, Trz2-A or Trz3-A.

[0047] Preferably, the host material is at least one of the specific compounds shown in TRZ-1 to TRZ-48;

[0048]

[0049]

[0050]

[0051] Preferably, the doping material in the organic electroluminescent composition is a boron nitrogen-porphyrin compound as described in any one of claims 1-3, and the host material is composed of any one of the compounds shown in formulas TRZ-1 to TRZ-48;

[0052] Preferably, the doping material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-48, and the host material is composed of any one of the compounds shown in formula TRZ-1 to TRZ-48.

[0053] On the other hand, the present invention provides an organic electroluminescent material, which includes boron nitrogen-porphyrin compounds or organic electroluminescent compositions as described above.

[0054] On the other hand, the present invention provides an organic electroluminescent device comprising an anode and a cathode and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising a boron nitrogen-porphyrin compound or an organic electroluminescent composition as described above.

[0055] Preferably, the organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, and an optional electron injection layer, wherein at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer comprises a boron nitride-porphyrin compound or an organic electroluminescent composition as described above.

[0056] In this invention, the organic electroluminescent composition can be used as a functional material in at least one of the following layers of an organic electroluminescent device: the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer.

[0057] In one embodiment of the present invention, the material of the light-emitting layer in the organic electroluminescent device comprises the boron nitride-porphyrin compound or organic electroluminescent composition as described above.

[0058] In one embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on energy transfer from the host material to any of the compounds shown in Formula I and Formula II or carrier capture of the light-emitting material itself.

[0059] In one embodiment of the present invention, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes a light-emitting layer containing the organic electroluminescent composition as described above, and may also include any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0060] On the other hand, the present invention provides an application of the described organic electroluminescent device in an organic electroluminescent display or an organic electroluminescent lighting source.

[0061] Terminology Explanation

[0062] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains.

[0063] As used herein, the terms “containing” or “including (comprise)” can be open-ended, semi-closed, or closed. In other words, the terms also include “consistently made of” or “composed of”.

[0064] Group definition

[0065] In this specification, groups and their substituents may be selected by those skilled in the art to provide stable structural moieties and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the structural formula is written from right to left.

[0066] The chapter headings used in this specification are for organizational purposes only and should not be construed as limiting the subject matter. All references or portions thereof cited in this invention, including but not limited to patents, patent applications, articles, books, user manuals, and papers, are incorporated herein by reference in their entirety.

[0067] Unless otherwise specified, all technical and scientific terms used herein have the standard meaning in the field to which the claimed subject matter pertains. Where multiple definitions exist for a term, the definition herein shall prevail.

[0068] It should be understood that the singular forms used in this invention, such as "a," include plural references unless otherwise specified. Furthermore, the term "comprising" is an open-ended limitation, not a closed one; that is, it includes the contents specified in this invention but does not exclude other aspects.

[0069] Unless otherwise stated, this invention employs traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can be referred to conventional operating procedures and conditions in the field.

[0070] Unless otherwise specified, this invention employs standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, organic synthetic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.

[0071] The compounds of the present invention may contain atomic isotopes in non-natural proportions on one or more atoms constituting the compound. For example, the compounds may be labeled with radioactive isotopes, such as deuterium (₂H). All variations in the isotopic composition of the compounds of the present invention, regardless of radioactivity, are included within the scope of the present invention.

[0072] In this invention, unless otherwise specified, the number of "substitutes" can be one or more; when there are multiples, it means two or more, such as two, three, or four. Furthermore, when there are multiple "substitutes," the "substitutes" can be the same or different. In this invention, unless otherwise specified, the position of the "substitute" can be arbitrary.

[0073] In this invention, as a group or part of other groups (e.g., in halogen-substituted alkyl groups), the term "alkyl" means a saturated aliphatic hydrocarbon group comprising branched and straight chains having a specified number of carbon atoms. For example, C1-C1... 20 Alkyl groups include straight-chain or branched alkyl groups having 1 to 20 carbon atoms. As defined in "C1-C6 alkyl," it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight-chain or branched structure. For example, in this invention, each of the C1-C6 alkyl groups is independently methyl, ethyl, propyl, butyl, pentyl, or hexyl; wherein, propyl is a C3 alkyl group (including isomers, such as n-propyl or isopropyl); butyl is a C4 alkyl group (including isomers, such as n-butyl, sec-butyl, isobutyl, or tert-butyl); pentyl is a C5 alkyl group (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1-butyl, isopentyl, tert-pentyl, or neopentyl); and hexyl is a C6 alkyl group (including isomers, such as n-hexyl or isohexyl).

[0074] As used herein, the term "alkoxy" refers to an alkyl group as defined above, which is connected via an oxygen bond (-O-).

[0075] In this invention, as a group or part of other groups, the term "Cn-m aryl" refers to a monocyclic or polycyclic aromatic group (with only carbon atoms as ring atoms) having n to m ring carbon atoms, possessing at least one carbon ring with a conjugated π-electron system. Examples of the aforementioned aryl unit include phenyl, naphthyl, indene, azulel, fluorenyl, phenanthryl, or anthraceneyl. In one embodiment, the aryl group is preferably a C6-14 aryl group, such as phenyl and naphthyl, more preferably phenyl.

[0076] In this invention, as a group or part of other groups, the term "nm-aryl" refers to an aromatic group whose ring atoms comprise one or more (e.g., 1, 2, 3, and 4) heteroatoms selected from nitrogen, oxygen, and sulfur, having n to m ring atoms. The heteroaryl group is a monocyclic, bicyclic, tricyclic, or tetracyclic system, wherein at least one ring is an aromatic ring. Heteroaryl groups within this definition include, but are not limited to: acridinel, carbazolyl, cyclophosphinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furanyl, thiophene, benzothiophene, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridinyl, pyrimidinel, pyrroleyl, tetrahydroquinoline, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazolyl, thiadiazolyl, etc. Oxadiazole, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, purine, pteridinyl, naphridinyl, quinazolinyl, phthalazinyl, imidazopyridinyl, imidazothiazolyl, imidazooxazinyl, benzothiazolyl, benzooxazinyl, benzoimidazolyl, isoindolyl, indazole, pyrrolopyridinyl, thienopyridinyl, furanolopyridinyl, benzothiadiazole, benzooxadiazole, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, as preferred examples of "5- to 18-membered heteroaryl groups", furanyl, thienoyl, pyrrololyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyrimidinyl, and carbazoleyl are listed, more preferably carbazoleyl.

[0077] As used herein, the term Cn-Cm cycloalkyl refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as 3-C10 cycloalkyl and C3-C6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and dicycloheptyl. In one embodiment, the C3-C10 cycloalkyl group is preferably adamantyl or cyclohexyl.

[0078] In this invention, the defined carbon number range of the group refers to any integer number of carbon atoms included within the defined range, such as C1 to C2. 20 This refers to the fact that the number of carbon atoms in the stated group can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, C3-C. 10 This means that the number of carbon atoms in the group can be 3, 4, 5, 6, 7, 8, 9 or 10, and the range of carbon atoms for other groups can be deduced similarly.

[0079] Without violating common sense in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain various preferred embodiments of the present invention.

[0080] The reagents and raw materials used in this invention are all commercially available.

[0081] Compared with the prior art, the present invention has the following beneficial effects:

[0082] The boron-nitrogen-porphyrin compound of the present invention has luminescent properties and is used as a luminescent material to prepare the luminescent layer of an organic electroluminescent device. The organic electroluminescent device prepared thereby can emit light under electrical drive, and the highest external quantum efficiency of the device is as high as 10% or more. Attached Figure Description

[0083] Figure 1 The diagram shows the device structure used in Examples 1-2, where 1 is the ITO anode, 2 is the hole injection layer, 3 is the hole transport layer, 4 is the light-emitting layer, 5 is the electron transport layer, 6 is the electron injection layer, and 7 is the metal cathode.

[0084] Figure 2 This is the photoluminescence spectrum of compound BN-1.

[0085] Figure 3 This is the photoluminescence spectrum of compound BN-2.

[0086] Figure 4 This is the photoluminescence spectrum of compound BN-5.

[0087] Figure 5 This is the photoluminescence spectrum of compound BN-6. Detailed Implementation

[0088] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0089] Representative examples of molecule synthesis are described below:

[0090] Synthesis of BN-1:

[0091]

[0092] Under a nitrogen atmosphere, 300 mg of raw material 5-(4-bromophenyl)-10,15,20-triphenylporphyrin (0.43 mmol), 398.5 mg of raw material tert-butylcarbazole boron ester (DtCzB-Bpin) (0.52 mmol), and 182.6 mg of potassium phosphate (0.86 mmol) were added to a mixed solution of 10 mL toluene, 0.5 mL ethanol, and 1 mL water. The mixture was bubbled with nitrogen for 5 minutes. Under a nitrogen atmosphere, 30 mg of tris(dibenzylideneacetone)dipalladium and 60 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum by heating. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a brownish-red solid product BN-1, in 20% yield. Mass spectrometry determined the molecular weight to be 1252.86 (theoretical value: 1252.63), and elemental analysis showed C 86.57%, H 6.16%, N 6.68% (theoretical values: C 86.24%, H 6.19%, N 6.70%). Synthesis of BN-2:

[0093]

[0094] In the first step, under a nitrogen atmosphere, 400 mg of starting material 5-(4-bromophenyl)-10,15,20-triphenylporphyrin (0.58 mmol) and 533.6 mg of starting material zinc acetate (14.5 mmol) were added to 12 mL of N,N-dimethylformamide. The mixture was bubbled with nitrogen for 10 minutes, heated to 150 °C, and stirred for 5 hours. After the reaction system cooled to room temperature, the organic phase was evaporated to dryness under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a purple solid intermediate M-1 in 90% yield.

[0095] In the second step, under a nitrogen atmosphere, 390 mg of intermediate M-1 (0.52 mmol), 478 mg of starting material tert-butylcarbazole boronazine ester (DtCzB-Bpin) (0.62 mmol), and 220.5 mg of potassium phosphate (1.04 mmol) were added to a mixed solution of 12 mL toluene, 0.5 mL ethanol, and 1.2 mL water. The mixture was bubbled with nitrogen for 5 minutes. Then, under a nitrogen atmosphere, 39 mg of tris(dibenzylacetone)dipalladium and 75 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a brownish-red solid product BN-2, with a yield of 19%. The molecular weight was determined by mass spectrometry to be 1316.13 (theoretical value: 1315.55), and the elemental analysis results were C 81.76%, H 5.71%, N: 6.35% (theoretical value: C 82.09%, H 5.74%, N: 6.38%).

[0096] Synthesis of BN-3

[0097]

[0098] In the first step, under a nitrogen atmosphere, 1.2 g of platinum dichloride (4.64 mmol) was added to 15 ml of benzonitrile. The system was bubbled with nitrogen for 10 minutes. The mixture was heated to 190 °C and stirred for 30 minutes. After cooling to room temperature, 400 mg of 5-(4-bromophenyl)-10,15,20-triphenylporphyrin (0.58 mmol) was added to the reaction system under a nitrogen atmosphere. The system was bubbled with nitrogen for 10 minutes. The mixture was heated to 190 °C and stirred for 8 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain orange solid intermediate M-2, yield: 70%.

[0099] In the second step, under a nitrogen atmosphere, 340 mg of intermediate M-2 (0.38 mmol), 353.1 mg of starting material tert-butylcarbazole boronazine ester (DtCzB-Bpin) (0.46 mmol), and 161.1 mg of potassium phosphate (0.76 mmol) were added to a mixed solution of 10 mL toluene, 0.5 mL ethanol, and 1 mL water. The mixture was bubbled with nitrogen for 5 minutes. Then, under a nitrogen atmosphere, 34 mg of tris(dibenzylacetone)dipalladium and 68 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain the orange solid product BN-3, yield: 5%. The molecular weight was determined by mass spectrometry to be 1446.21 (theoretical value: 1446.58), and the elemental analysis results were C 74.25%, H 5.27%, N: 5.78% (theoretical value: C 74.73%, H 5.23%, N: 5.81%).

[0100] Synthesis of BN-5:

[0101]

[0102] Under a nitrogen atmosphere, 300 mg of raw material 5-(3-bromophenyl)-10,15,20-triphenylporphyrin (0.43 mmol), 398.5 mg of raw material tert-butylcarbazole boron ester (DtCzB-Bpin) (0.52 mmol), and 182.6 mg of potassium phosphate (0.86 mmol) were added to a mixed solution of 10 mL toluene, 0.5 mL ethanol, and 1 mL water. The mixture was bubbled with nitrogen for 5 minutes. Under a nitrogen atmosphere, 30 mg of tris(dibenzylideneacetone)dipalladium and 60 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum by heating. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a brownish-red solid product BN-5 in 16% yield. The molecular weight was determined to be 1252.51 (theoretical value: 1252.63) by mass spectrometry, and the elemental analysis results were C 86.01%, H 6.15%, N: 6.73% (theoretical values: C 86.24%, H 6.19%, N: 6.70%).

[0103] Synthesis of BN-6

[0104]

[0105] In the first step, under a nitrogen atmosphere, 400 mg of starting material 5-(3-bromophenyl)-10,15,20-triphenylporphyrin (0.58 mmol) and 533.6 mg of starting material zinc acetate (14.5 mmol) were added to 12 mL of N,N-dimethylformamide. The mixture was bubbled with nitrogen for 10 minutes, heated to 150 °C, and stirred for 5 hours. After the reaction system cooled to room temperature, the organic phase was evaporated to dryness under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a purple solid intermediate M-3 in 90% yield.

[0106] In the second step, under a nitrogen atmosphere, 390 mg of intermediate M-3 (0.52 mmol), 478 mg of starting material tert-butylcarbazole boronazine ester (DtCzB-Bpin) (0.62 mmol), and 220.5 mg of potassium phosphate (1.04 mmol) were added to a mixed solution of 12 mL toluene, 0.5 mL ethanol, and 1.2 mL water. The mixture was bubbled with nitrogen for 5 minutes. Then, under a nitrogen atmosphere, 39 mg of tris(dibenzylacetone)dipalladium and 75 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain a brownish-red solid product BN-6, with a yield of 15%. The molecular weight was determined by mass spectrometry to be 1315.67 (theoretical value: 1315.55), and the elemental analysis results were C 82.39%, H 5.75%, N: 6.37% (theoretical value: C 82.09%, H 5.74%, N: 6.38%).

[0107] Synthesis of BN-7:

[0108]

[0109] In the first step, under a nitrogen atmosphere, 1.2 g of platinum dichloride (4.64 mmol) was added to 15 ml of benzonitrile. The system was bubbled with nitrogen for 10 minutes. The mixture was heated to 190 °C and stirred for 30 minutes. After cooling to room temperature, 400 mg of 5-(3-bromophenyl)-10,15,20-triphenylporphyrin (0.58 mmol) was added to the reaction system under a nitrogen atmosphere. The system was bubbled with nitrogen for 10 minutes. The mixture was heated to 190 °C and stirred for 8 hours. After the reaction system cooled to room temperature, the organic phase was dried under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain orange solid intermediate M-4, yield: 70%.

[0110] In the second step, under a nitrogen atmosphere, 340 mg of intermediate M-2 (0.38 mmol), 353.1 mg of starting material tert-butylcarbazole boronazine ester (DtCzB-Bpin) (0.46 mmol), and 161.1 mg of potassium phosphate (0.76 mmol) were added to a mixed solution of 10 mL toluene, 0.5 mL ethanol, and 1 mL water. The mixture was bubbled with nitrogen for 5 minutes. Then, under a nitrogen atmosphere, 34 mg of tris(dibenzylacetone)dipalladium and 68 mg of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added. The mixture was bubbled with nitrogen again for 5 minutes. The mixture was then heated to 90 °C and stirred for 12 hours. After the reaction system cooled to room temperature, the organic phase was evaporated under vacuum. The reaction mixture was extracted with dichloromethane and water, and then purified by column chromatography and recrystallization to obtain the orange solid product BN-7. The molecular weight was determined by mass spectrometry to be 1446.86 (theoretical value: 1446.58), and the elemental analysis results were C 74.31%, H 5.20%, N: 5.84% (theoretical values: C 74.73%, H 5.23%, N: 5.81%).

[0111] Figure 2 The image shows the photoluminescence spectrum of compound BN-1, with the main emission peak at 655 nm.

[0112] Figure 3 The image shows the photoluminescence spectrum of compound BN-2, with the main emission peak at 648 nm.

[0113] Figure 4 The image shows the photoluminescence spectrum of compound BN-5, with the main emission peak at 652 nm.

[0114] Figure 5 The image shows the photoluminescence spectrum of compound BN-6, with the main emission peak at 648 nm.

[0115] Examples of electroluminescent devices

[0116] The following are some representative examples of electroluminescent devices. The molecular structures of some materials involved in these device examples are as follows:

[0117]

[0118] The following are examples of electroluminescent devices fabricated using the materials of the present invention, and the specific device fabrication process is as follows:

[0119] (1) Substrate treatment: Transparent ITO glass was used as the substrate material for device fabrication. It was first ultrasonically treated with 5% ITO cleaning solution for 30 minutes, then sequentially ultrasonically washed with distilled water (twice), acetone (twice), and isopropanol (twice). Finally, the ITO glass was stored in isopropanol. Before each use, the surface of the ITO glass was carefully wiped with acetone and isopropanol cotton balls, rinsed with isopropanol, dried, and then plasma-treated for 5 minutes before use. Device fabrication was completed using a combination of spin coating and vacuum evaporation processes.

[0120] (2) Preparation of hole injection layer and hole transport layer: First, a 20 nm thick layer of PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrene sulfonate) was spin-coated on the ITO surface as a hole injection layer. Then, a 50 nm thick layer of Poly-HTL was spin-coated on the hole injection layer as a hole transport layer. Then, the ITO glass with the hole injection layer and the hole transport layer was placed in a glove box under nitrogen protection and annealed at 200 °C for 30 minutes (to allow Poly-HTL to crosslink).

[0121] (3) Preparation of luminescent layer: The main material and the luminescent material are dissolved in xylene at a ratio of 99wt%:1wt% (wt% is the weight percentage concentration) to prepare a solution with a concentration of 2wt%. The luminescent layer is prepared by spin coating using the prepared solution. The thickness of the luminescent layer is 50nm.

[0122] (4) Fabrication of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are fabricated using a vapor deposition process. When the vacuum degree of the vacuum deposition system reaches 5×10 -4 Vapor deposition begins when the pressure is below a certain level (Pa). The deposition rate is measured using a SAINS film thickness gauge. An organic electron transport layer, a LiF electron injection layer, and a metal Al electrode are sequentially deposited on the light-emitting layer using a vacuum evaporation process (see the following effect example for specific device structure). The deposition rate of the organic material is [missing information - likely a specific value]. The deposition rate of LiF is The deposition rate of Al is Device Examples E1-E2

[0123] Organic electroluminescent devices (structure as shown in device embodiments E1-E2) Figure 1In the example shown, PEDOT:PSS is used as the hole injection layer, Poly-HTL is used as the hole transport layer, TRZ-41 is used as the host material in the light-emitting layer, BN-2 and BN-6 are used as doped light-emitting materials (doping concentration of 1wt%), TRZ-28 is used as the electron transport material, LiF is used as the electron injection layer, and Al is used as the metal cathode. The structure of the organic electroluminescent device in the example is [ITO / PEDOT:PSS (20nm) / Poly-HTL (50nm) / 99wt% TRZ-41 + 1wt% BN-2 or BN-6 / TRZ-28 (50nm) / LiF (1nm) / Al (100nm)].

[0124] The device's current, voltage, luminance, and emission spectrum characteristics were simultaneously tested using a Photo Research PR 655 spectrophotometer and a Keithley K2400 digital source meter system. Performance testing was conducted at room temperature and under ambient conditions. The external quantum efficiency (EQE) of the device was calculated based on the Lambaugh distribution of emission, using current density, luminance, and electroluminescence spectrum combined with the apparent function.

[0125] The test results are shown in Table 1.

[0126] Table 1

[0127]

[0128] The applicant declares that the present invention is illustrated by the above embodiments to demonstrate the boron-nitrogen-porphyrin compound and its application, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A boron-nitrogen-porphyrin compound, characterized in that, The boron-nitrogen-porphyrin compound has the structure shown in Formula I or Formula II: M represents Zn +2 , Pt +2 , Pd +2 , Ru +2 , Os +2 , Cu +2 , Fe +2 , Co +2 , [AlCl] +2 , [GaCl] +2 , [RuCl] +2 , [OsCl] +2 , [IrCl] +2 , [FeCl] +2 , [CoCl] +2 , [LaCl] +2 , [AlOH] +2 , [GaOH +2 , [RuF] +2 , [OsF] +2 , [IrF] +2 , [FeF] +2 , [CoF] +2 or [LaF] +2 ; R 1 R 2 R 3 and R 4 Independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl, and dominated by one or more R a Substituted C6-C18 aryl, 5- to 18-heteroaryl, and substituted with one or more R a Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R a Substituted diphenylamine group; R a Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. b Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R b Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R b Substituted diphenylamine group; R b Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. c Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R c Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R c Substituted diphenylamine group; R c Each occurrence is independently of deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, and is accompanied by one or more R. d Substituted C6-C14 aryl, 5- to 18-membered heteroaryl, and substituted with one or more R d Substituted 5- to 18-membered heteroaryl, diphenylamino, or substituted with one or more R d Substituted diphenylamine group; R d Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl, or is affected by one or more R groups. e Substituted C6-C14 aryl groups; R e Each time it appears, it is independently deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 1 R 2 R 3 and R 4 Independent existence or R 1 R 2 R 3 and R 4 At least one of them forms a ring with the connected aromatic ring; R P1 R P2 R P3 R P4 R P5 R P6 and R P7 It is H, deuterium, F, C1-C18 alkyl, C6-C14 aryl, 5- to 24-membered heteroaryl or The asterisks represent bond sites; R P1 R P2 R P3 R P4 R P5 R P6 and R P7 Independent existence or R P1 R P2 R P3 R P4 R P5 R P6 and R P7 At least one of them forms a ring with the connected aromatic ring; The alkyl, alkoxy, cycloalkyl, aryl, or heteroaryl groups may be optionally substituted with one or at least two substituents selected from the following: halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5- to 18-membered heteroaryl.

2. The boron-nitrogen-porphyrin compound according to claim 1, characterized in that, The R 1 R 2 R 3 and R 4 Independently H, deuterium, C1-C12 alkyl, C1-C 12 Alkoxy, C3-C 10 Cycloalkyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R a Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R b Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R c Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, phenyl-C1~C 12 Alkyl, diphenylamino, with at least one C1-C 12 Alkyl-substituted diphenylamino group, carbazole group, or group with at least one C1-C 12 Alkyl-substituted carbazole group; Preferably, the R d Each occurrence is independent of deuterium, fluorine, and C1-C2. 12 Alkyl, C1-C 12 Alkoxy, C3-C 10 cycloalkyl, with at least one C1-C 12 Alkyl-substituted phenyl, with at least one C1-C 12 Alkoxy-substituted phenyl, carbazole, or alkyl-substituted phenyl groups with at least one C1-C bond 12 Alkyl-substituted carbazole group; Preferably, the R 1 R 2 R 3 and R 4 Independently, it is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexoxy Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl The wavy lines represent the connection sites of the functional groups; Preferably, the R 1 R 2 R 3 and R 4 Independently hydrogen, methyl, 2-methyl-phenyl, Phenyl, The wavy lines represent the connection sites of the functional groups; More preferably, the R 1 R 2 R 3 and R 4 Independently for hydrogen, Preferably, R P1 R P2 R P3 R P4 R P5 R P6 and R P7 It is H, deuterium, methyl or tert-butyl.

3. The boron-nitrogen compound according to claim 1 or 2, characterized in that, The boron-nitrogen-porphyrin compound is any one of the following compounds:

4. An organic electroluminescent composition, characterized in that, The organic electroluminescent composition comprises a host material and a dopant material, wherein the dopant material comprises any one of claims 1-3 boron nitride porphyrin compounds; Preferably, the host material is a material having electron transport capability and / or hole transport capability and whose triplet excited state energy is equal to or higher than the triplet excited state energy of the doped material.

5. The organic electroluminescent composition according to claim 4, characterized in that, The doping material in the organic electroluminescent composition is any one of the boron nitrogen-porphyrin compounds according to any one of claims 1-3; the host material is any one of the compounds shown as Trz1-A, Trz2-A or Trz3-A; Z is either N or CH; Where R z1 As for R z10 Independently hydrogen, deuterium, F, CN, C1-C8 alkyl, C1-C8 alkoxy, C6-C 30 Aryl, R za Replacement C6-C 30 Aryl, C6-C30 heteroaryl or R za β-substituted C6-C 30 Mixed aromatics; R za It is a C1-C8 alkyl, C1-C8 alkoxy, C6-C 24 Aryl or C6-C 24 Mixed aromatics; R z9 Or R z10 Aromatic rings, either independently or connected to them, form a ring; Preferably, the organic electroluminescent composition contains 0.3wt-15.0wt% doped material and 99.7wt-85.0wt% main material by weight. Preferably, the doping material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-48, and the host material is composed of any one of the compounds shown in formula Trz1-A, Trz2-A or Trz3-A. Preferably, the host material is at least one of the specific compounds shown in TRZ-1 to TRZ-48: Preferably, the doping material in the organic electroluminescent composition is a boron nitrogen-porphyrin compound as described in any one of claims 1-3, and the host material is composed of any one of the compounds shown in formulas TRZ-1 to TRZ-48; Preferably, the doping material in the organic electroluminescent composition is any one of the compounds described in BN-1 to BN-48, and the host material is composed of any one of the compounds shown in formula TRZ-1 to TRZ-48.

6. An organic electroluminescent material, characterized in that, The organic electroluminescent material includes any one of the boron-nitrogen-porphyrin compounds as described in claims 1-3 or the organic electroluminescent composition as described in claims 4 or 5.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises an anode and a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer comprising a boron nitrogen-porphyrin compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic thin film layer includes a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, and an optional electron injection layer, wherein at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer comprises a boron nitride-porphyrin compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5.

9. The organic electroluminescent device according to claim 7 or 8, characterized in that, The material of the light-emitting layer in the organic electroluminescent device comprises a boron nitride-porphyrin compound as described in any one of claims 1-3 or an organic electroluminescent composition as described in claim 4 or 5; Preferably, the organic electroluminescent device further includes an optional hole blocking layer, an optional electron blocking layer, and an optional capping layer.

10. The application of the organic electroluminescent device according to any one of claims 7-9 in an organic electroluminescent display or an organic electroluminescent lighting source.

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